Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and - cycloheptanols

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1-5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent.

Original languageEnglish
Pages (from-to)1985-1993
Number of pages9
JournalTetrahedron Asymmetry
Volume10
Issue number10
DOIs
Publication statusPublished - May 21 1999

Fingerprint

Lipases
Lipase
Ethers
acetylation
acylation
Acetylation
Acylation
diethyl ether
Enantioselectivity
Ether
Reaction rates
esters
acetates
ethers
Esters
Screening
reaction kinetics
screening
rings
diisopropyl ether

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and - cycloheptanols. / Forró, E.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 10, No. 10, 21.05.1999, p. 1985-1993.

Research output: Contribution to journalArticle

@article{69e647032ebc49a19492f4a100884d2c,
title = "Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and - cycloheptanols",
abstract = "Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1-5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent.",
author = "E. Forr{\'o} and F. F{\"u}l{\"o}p",
year = "1999",
month = "5",
day = "21",
doi = "10.1016/S0957-4166(99)00189-5",
language = "English",
volume = "10",
pages = "1985--1993",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and - cycloheptanols

AU - Forró, E.

AU - Fülöp, F.

PY - 1999/5/21

Y1 - 1999/5/21

N2 - Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1-5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent.

AB - Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1-5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent.

UR - http://www.scopus.com/inward/record.url?scp=0345711495&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0345711495&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(99)00189-5

DO - 10.1016/S0957-4166(99)00189-5

M3 - Article

VL - 10

SP - 1985

EP - 1993

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 10

ER -